IMPPAT Phytochemical information: 
Cycleanine

Cycleanine
Summary

SMILES: COc1c(OC)cc2c3c1Oc1ccc(cc1)C[C@H]1N(C)CCc4c1c(Oc1ccc(C[C@H]3N(CC2)C)cc1)c(c(c4)OC)OC
InChI: InChI=1S/C38H42N2O6/c1-39-17-15-25-21-31(41-3)35(43-5)37-33(25)29(39)19-23-7-11-28(12-8-23)46-38-34-26(22-32(42-4)36(38)44-6)16-18-40(2)30(34)20-24-9-13-27(45-37)14-10-24/h7-14,21-22,29-30H,15-20H2,1-6H3/t29-,30-/m1/s1
InChIKey: ANOXEUSGZWSCQL-LOYHVIPDSA-N
DeepSMILES: COccOC))cccc6Occcccc6))C[C@H]NC)CCcc6cOccccC[C@H]%22NCC%26))C))))cc6)))))))ccc6)OC)))OC
Scaffold Graph/Node/Bond level: c1cc2c3c(c1)Oc1ccc(cc1)CC1NCCc4cccc(c41)Oc1ccc(cc1)CC3NCC2
Scaffold Graph/Node level: C1CC2CCNC3CC4CCC(CC4)OC4CCCC5CCNC(CC6CCC(CC6)OC(C1)C23)C54
Scaffold Graph level: C1CC2CCCC3CC4CCC(CC4)CC4CCCC5CCCC(CC6CCC(CC6)CC(C1)C23)C54
Functional groups: cOC; CN(C)C; cOc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Ethers
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
cycleanine, Cycleanine
External chemical identifiers:
CID:CID_121313; ChEMBL:CHEMBL443389; ChEBI:CHEBI:81051; ZINC:ZINC000044281044; FDASRS:BN8R5T4KQ9; SureChEMBL:SCHEMBL21974
Chemical structure download


Cycleanine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 622.76
Log P RDKit 7.16
Topological polar surface area (Å2) RDKit 61.86
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 38
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.37
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 6
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 10
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 10


Cycleanine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.24


Cycleanine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.37
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No